We report a case of a metastatic cutaneous melanoma to the orbit. A 60-year-old Caucasian male presented with a 2-day history of left-sided ocular pain, lid swelling and chemosis. Initially, this was treated as conjunctivitis with no signs of improvement. Four days later, the patient developed left proptosis, mechanical ptosis, left esotropia and diplopia. Computed tomography scan of the orbit demonstrated marked thickening of the lateral rectus muscle. The patient was treated as pseudotumor. Subsequent biopsy revealed malignant cutaneous melanoma. The patient had a history of cutaneous melanoma excised 15 years previously. Further imaging showed advanced metastatic disease in the brain, the lung and the liver. The patient passed away five months after initial presentation. Cutaneous melanoma metastasizing to the orbit has poor prognosis. Patients often have advanced disease at the time of presentation and orbital metastases may be the initial sign. A detailed history is paramount in making timely diagnosis.